WO1984000095A1 - Formules parasiticides - Google Patents

Formules parasiticides Download PDF

Info

Publication number
WO1984000095A1
WO1984000095A1 PCT/GB1983/000166 GB8300166W WO8400095A1 WO 1984000095 A1 WO1984000095 A1 WO 1984000095A1 GB 8300166 W GB8300166 W GB 8300166W WO 8400095 A1 WO8400095 A1 WO 8400095A1
Authority
WO
WIPO (PCT)
Prior art keywords
formulation according
formulation
levamisole
cypermethrin
uherein
Prior art date
Application number
PCT/GB1983/000166
Other languages
English (en)
Inventor
John Mckeller Ballany
Andrew Galbraith
Original Assignee
Young Robert Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Young Robert Co Ltd filed Critical Young Robert Co Ltd
Publication of WO1984000095A1 publication Critical patent/WO1984000095A1/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/22—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing ingredients stabilising the active ingredients
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles

Definitions

  • This invention relates to parasiticidal formulations which are useful in eradicating and/or controlling both endo- and ectoparasites which attack warm-blooded non-human animals.
  • animals such as sheep and cattle can be simultaneously infested under certain conditions uith both endoparasites, including for example helminths such as gut and lungw ⁇ rms and ectoparasites including for example lice, keds, mites, ticks and fleas.
  • helminths such as gut and lungw ⁇ rms
  • ectoparasites including for example lice, keds, mites, ticks and fleas.
  • known insecticides are selective in being either endoparasiticidal or ectoparasiticidal and if it is desired to control both types of parasite then separate applications of the insecticides are usually necessary.
  • cypermethrin NRDC 149
  • NRDC 149 whose preparation is described in UK patent No. 1,413,491.
  • the term cypermethrin is used herein to embrace all isomers of: ⁇ - cyano -3-phenocyphenyl (-) -cis, trans -2,2- dimethyl-3-(2, 2-dichloro ⁇ inyl) -cydopropanecarboxylate
  • cypermethrin as a pour-on formulation for controlling ectoparasites and blowfly myiasis is described in our copending application No. 8205879.
  • tetramisole (2,3,5,6 - tetrahydro-6-phenylimidazo-2, 1-6thiazole) and its laevo isomer levamisole.
  • Tetramisole and levamisole are described in UK patent No. 1,043,489.
  • a further object is to provide a pour-on or spot-on endo- and ectoparasiticidal formulation of cypermethrin and levamisole (or tetramisole) in a suitable solvent and which retains useful or unimpaired efficacy against parasites after storage of the formulation for a prolonged period e.g. greater than one year.
  • a parasiticidal formulation which comprises a mixture of items (i) to (iii) below in a suitable solvent: (i) cypermethrin, (ii) levamisole, and (iii) an amount of a soluble acid effective in retarding or preventing decomposition of either
  • parasites are meant to include endo parasites, e.g. gut and lungworms, as well as ectoparasites, e.g. lice, keds, mites, ticks, fleas, blowfly.
  • controlling parasites is meant to include the interference with the development and/or the reproduction of said parasites.
  • unimpaired efficacy means that the formulations have an efficacy which is unimpaired in comparison with the efficacy of two compositions comprising the same amount of levamisole and cypermethrin separately.
  • useful efficacy means that the formulations have an efficacy greater than mixture which has undergone decomposition but less than unimpaired efficacy.
  • tetramisole may be used or a mixture of tetramisole and levamisole.
  • the preferred acids are optionally substituted aliphatic carb ⁇ xylic acids, either single acids or combinations of one or more and preferably having a pKa value in the range from 0.6 to 6.0.
  • Suitable acids are citric acid, acetic acid and malonic acid.
  • the acid(s) should be selected to minimise any irritation to the animal and maximise stability.
  • the solvents selected for the formulations of the invention may be known insecticidal solvents.
  • Selection is based on the criteria:- a) ability to dissolve both actives, and the stabilising acids, b) ability to facilitate the spread of the cypermethrin across the skin surface of the target species, c) ability to facilitate penetration of the levamisole through the skin of the target species, d) avoidance of significant adverse skin reactions on the target species, e) avoidance of troublesome properties such as toxicity, inflammability, unacceptable odou , high freezing point.
  • the solvent choice for c) and d) will depend on the target species as a solvent system with no drawbacks on cattle may not be acceptable for treatment of sheep, and vice-versa. Also it is unlikely that one single solvent will meet all the above criteria.
  • etheralcohols such as butyl dioxitol, monoterpenes containing hydrocarbon and ether functions such as eucalyptus oil and terpinolene, and polar oxygenated solvents such as dimethyl sulphoxide and dimethylformamide.
  • BHT butylated hydroxy toluene
  • ingredients can be dissolved in one or more alcohols of formula:-
  • the solvent may comprise & majror part of this alcohol which exhibits excellent spreading and absorbtion characteristics.
  • Cypermethrin will be used in most instances at between 21 ⁇ 2-10 mg/kg liveweight, depending on the species and parasite, with levamisole used at 5-15 mg/kg liveweight. This gives guidance on choice of active ratio and concentrations as below:- Active Ratio
  • Cypermethrin/Levamisole will normally be used between the ratios 1:4 and 1:1, depending on the species and the parasite under attack. Concentration
  • Solubility may again impose limits, but up to
  • the mixture formed a clear homogenous solution, effective in controlling both ectoparasites and endoparasites on cattle, and without sign of unuanted side effects. Stability indications were satisfactory, and shelf-life expectation is high.
  • the active ratio may be 1 cypermethrin: 2 levamisole.
  • a maximum concentration may be 10% w/v cypermethrin:
  • the solvent may include oxygenated compounds such as glycols, ethers and esters. Acid proportions may be up to 20% w/v for malonic or citric acid and up to 10% w/v acetic acid.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Agronomy & Crop Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Toxicology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Une formule parasiticide et une méthode de contrôle des endo et/ou ectoparasites sur des animaux comprennent de la cyperméthrine et du levamisol dans un solvant approprié et dans lequel on ajoute un acide soluble pour stabiliser le mélange contre la décomposition pendant le stockage. On peut utiliser par exemple l'acide acétique ou l'acide malonique.
PCT/GB1983/000166 1982-07-02 1983-06-30 Formules parasiticides WO1984000095A1 (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB8219104 1982-07-02

Publications (1)

Publication Number Publication Date
WO1984000095A1 true WO1984000095A1 (fr) 1984-01-19

Family

ID=10531425

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1983/000166 WO1984000095A1 (fr) 1982-07-02 1983-06-30 Formules parasiticides

Country Status (6)

Country Link
EP (1) EP0112878A1 (fr)
AU (1) AU1611383A (fr)
GB (1) GB2122902B (fr)
IE (1) IE55205B1 (fr)
NZ (1) NZ204735A (fr)
WO (1) WO1984000095A1 (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0116401A2 (fr) * 1983-01-10 1984-08-22 Robert Young & Company Limited Compositions anti-endoparasitaires
WO1986007525A1 (fr) * 1985-06-19 1986-12-31 Robert Young & Company Limited Compositions parasiticides a base de pyrethroide
US4710083A (en) * 1984-10-29 1987-12-01 Johann Wolf Gesellschaft M.B.H. Kg Nailing plate for the production of compound supports, and compound support
EP0354761A2 (fr) * 1988-08-09 1990-02-14 CHINOIN Gyogyszer és Vegyészeti Termékek Gyára RT. Compositions vétérinaires pour emploi contre les endoparasites et leur procédé de préparation
WO1992003927A1 (fr) * 1990-09-12 1992-03-19 Perycut-Chemie Ag Produit insecticide
CN1044960C (zh) * 1996-09-18 1999-09-08 中国农业科学院植物保护研究所 苦参碱氯氰菊酯混剂及其制造方法
US6340672B1 (en) * 2000-02-16 2002-01-22 Phoenix Scientific, Inc. Parasiticidal formulation and a method of making this formulation
WO2010030501A2 (fr) * 2008-09-12 2010-03-18 Dow Agrosciences Llc Compositions pesticides
US20100168177A1 (en) * 2008-12-26 2010-07-01 Dow Agrosciences, Llc Stable insecticide compositions

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8327761D0 (en) * 1983-10-17 1983-11-16 Janssen Pharmaceutica Nv Parasiticidal formulations
ES2157811B1 (es) 1998-07-29 2002-03-16 Sumitomo Chemical Co Preparado insecticida acuoso para fumigacion termica.

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1043489A (en) * 1964-05-11 1966-09-21 Janssen Pharmaceutica Nv Imidazo[2,1-b]thiazoles and process for preparing them
GB1413491A (en) * 1972-05-25 1975-11-12 Nat Res Dev 3-substituted-2,2-dimethyl-cyclopropane carboxylic acid esters their preparation and their use in pesticidal compositions
GB2058569A (en) * 1979-09-12 1981-04-15 Montedison Spa Liquid insecticide compositions containing synthetic pyrethroids
EP0042290A2 (fr) * 1980-06-17 1981-12-23 Janssen Pharmaceutica N.V. Une composition anthelmintique non toxique pour application topique
EP0045424A1 (fr) * 1980-08-02 1982-02-10 Bayer Ag Formulations "pour-on" actives contre les tiques
GB2094626A (en) * 1981-03-16 1982-09-22 Young Robert Co Ltd Insecticidal control of ectoparasites
EP0061806A1 (fr) * 1981-03-24 1982-10-06 Janssen Pharmaceutica N.V. Compositions non-irritantes de tétramisole ou lévamisole pour application externe
EP0074335A1 (fr) * 1981-09-03 1983-03-16 Ciba-Geigy Ag Formulations antimites stables à l'entreposage

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1043489A (en) * 1964-05-11 1966-09-21 Janssen Pharmaceutica Nv Imidazo[2,1-b]thiazoles and process for preparing them
GB1413491A (en) * 1972-05-25 1975-11-12 Nat Res Dev 3-substituted-2,2-dimethyl-cyclopropane carboxylic acid esters their preparation and their use in pesticidal compositions
GB2058569A (en) * 1979-09-12 1981-04-15 Montedison Spa Liquid insecticide compositions containing synthetic pyrethroids
EP0042290A2 (fr) * 1980-06-17 1981-12-23 Janssen Pharmaceutica N.V. Une composition anthelmintique non toxique pour application topique
EP0045424A1 (fr) * 1980-08-02 1982-02-10 Bayer Ag Formulations "pour-on" actives contre les tiques
GB2094626A (en) * 1981-03-16 1982-09-22 Young Robert Co Ltd Insecticidal control of ectoparasites
EP0061806A1 (fr) * 1981-03-24 1982-10-06 Janssen Pharmaceutica N.V. Compositions non-irritantes de tétramisole ou lévamisole pour application externe
EP0074335A1 (fr) * 1981-09-03 1983-03-16 Ciba-Geigy Ag Formulations antimites stables à l'entreposage

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0116401A2 (fr) * 1983-01-10 1984-08-22 Robert Young & Company Limited Compositions anti-endoparasitaires
EP0116401A3 (fr) * 1983-01-10 1985-08-07 Robert Young & Company Limited Compositions anti-endoparasitaires
US4710083A (en) * 1984-10-29 1987-12-01 Johann Wolf Gesellschaft M.B.H. Kg Nailing plate for the production of compound supports, and compound support
WO1986007525A1 (fr) * 1985-06-19 1986-12-31 Robert Young & Company Limited Compositions parasiticides a base de pyrethroide
EP0354761A2 (fr) * 1988-08-09 1990-02-14 CHINOIN Gyogyszer és Vegyészeti Termékek Gyára RT. Compositions vétérinaires pour emploi contre les endoparasites et leur procédé de préparation
EP0354761A3 (fr) * 1988-08-09 1991-05-08 CHINOIN Gyogyszer és Vegyészeti Termékek Gyára RT. Compositions vétérinaires pour emploi contre les endoparasites et leur procédé de préparation
WO1992003927A1 (fr) * 1990-09-12 1992-03-19 Perycut-Chemie Ag Produit insecticide
US5641499A (en) * 1990-09-12 1997-06-24 Franz Bencsits Insecticidal product
CN1044960C (zh) * 1996-09-18 1999-09-08 中国农业科学院植物保护研究所 苦参碱氯氰菊酯混剂及其制造方法
US6492340B2 (en) 2000-02-16 2002-12-10 Phoenix Scientific, Inc. Parasiticidal formulation and a method of making this formulation
US6340672B1 (en) * 2000-02-16 2002-01-22 Phoenix Scientific, Inc. Parasiticidal formulation and a method of making this formulation
AU2001236949B2 (en) * 2000-02-16 2006-08-17 Bayer Healthcare Animal Health Inc. A parasiticidal formulation and a method of making this formulation
WO2010030501A2 (fr) * 2008-09-12 2010-03-18 Dow Agrosciences Llc Compositions pesticides
WO2010030501A3 (fr) * 2008-09-12 2011-02-17 Dow Agrosciences Llc Compositions pesticides
US8178500B2 (en) 2008-09-12 2012-05-15 Dow Agrosciences Llc Pesticidal compositions
AU2009292044B2 (en) * 2008-09-12 2014-05-08 Corteva Agriscience Llc Stabilized pesticidal compositions
TWI471096B (zh) * 2008-09-12 2015-02-01 Dow Agrosciences Llc 殺蟲組成物
US20100168177A1 (en) * 2008-12-26 2010-07-01 Dow Agrosciences, Llc Stable insecticide compositions
CN104222135A (zh) * 2008-12-26 2014-12-24 美国陶氏益农公司 稳定的亚磺酰亚胺杀虫剂组合物
CN104222135B (zh) * 2008-12-26 2017-04-26 美国陶氏益农公司 稳定的亚磺酰亚胺杀虫剂组合物

Also Published As

Publication number Publication date
GB2122902A (en) 1984-01-25
IE831546L (en) 1984-01-02
EP0112878A1 (fr) 1984-07-11
NZ204735A (en) 1986-04-11
GB2122902B (en) 1985-05-01
IE55205B1 (en) 1990-07-04
AU1611383A (en) 1984-01-05
GB8316960D0 (en) 1983-07-27

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